Hydrochloric Acid → 4-Methoxy-2-(3',4',5'-tris(octadecyloxy)cyclohexylmethyloxy)benzyl alcohol

HRID 1502544Notes

Reaction equation

HRID 1502544 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[O:8])=[C:5]([O:11][CH2:12][CH:13]2[CH2:18][CH:17]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[CH:16]([O:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH3:56])[CH:15]([O:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH2:72][CH2:73][CH2:74][CH3:75])[CH2:14]2)[CH:4]=1.[BH4-].[Na+].Cl>C1COCC1.CO>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][OH:8])=[C:5]([O:11][CH2:12][CH:13]2[CH2:18][CH:17]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[CH:16]([O:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH3:56])[CH:15]([O:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH2:72][CH2:73][CH2:74][CH3:75])[CH2:14]2)[CH:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 866548934-Methoxy-2-(3',4',5'-tris(octadecyloxy)cyclohexylmethyloxy)benzaldehyde

Product 1

HCID 532589174-Methoxy-2-(3',4',5'-tris(octadecyloxy)cyclohexylmethyloxy)benzyl alcoholYield 97%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

4-Methoxy-2-(3′,4′,5′-tris(octadecyloxy)cyclohexylmethyloxy)benzaldehyde (73.56 g, 69.8 mmol) was dissolved in THF-methanol (1100 ml+55 ml), and sodium borohydride (3.17 g, 83.8 mmol) was added at 0° C. After stirring the mixture at room temperature for 1.5 hr, 0.2N hydrochloric acid (150 ml) was added at 0° C. to quench the reaction. The solvent was evaporated to about half, and the residue was dissolved in chloroform (1400 ml), washed twice with 0.1N hydrochloric acid (700 ml), and twice with pure water (700 ml). The solvent was evaporated, and the residue was precipitated with methanol (800 ml), and washed with acetonitrile (800 ml) to give 4-methoxy-2-(3′,4′,5′-tris(octadecyloxy)cyclohexylmethyloxy)benzyl alcohol (71.5 g, 67.7 mmol, 92% vs methyl 3,4,5-tris(octadecyloxy)cyclohexylcarboxylate).

Workup

  1. customto quench
  2. customthe reaction
  3. customThe solvent was evaporated to about half
  4. dissolutionthe residue was dissolved in chloroform (1400 ml)
  5. washwashed twice with 0.1N hydrochloric acid (700 ml)
  6. customThe solvent was evaporated
  7. customthe residue was precipitated with methanol (800 ml)
  8. washwashed with acetonitrile (800 ml)

Sources & evidence

ORD record
ord-4a43524260944e31a41c217e18d4dc57
Source dataset
uspto-grants-2015_12
Patent number
US09206230B2

Reaction notes

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