Hydrochloric Acid → 2-(3',5'-Di(docosyloxy)benzyl)-4-methoxybenzyl alcohol

HRID 537604Notes

Reaction equation

HRID 537604 reaction equation
[CH2:1]([O:23][C:24]1[CH:25]=[C:26]([CH:38]=[C:39]([O: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][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH3:63])[CH:40]=1)[CH2:27][C:28]1[CH:35]=[C:34]([O:36][CH3:37])[CH:33]=[CH:32][C:29]=1[CH:30]=[O:31])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].[BH4-].[Na+].Cl>C1COCC1.CCO>[CH2:42]([O:41][C:39]1[CH:38]=[C:26]([CH:25]=[C:24]([O:23][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH:40]=1)[CH2:27][C:28]1[CH:35]=[C:34]([O:36][CH3:37])[CH:33]=[CH:32][C:29]=1[CH2:30][OH:31])[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][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH3:63]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 866548892-(3',5'-Di(docosyloxy)benzyl)-4-methoxybenzaldehyde

Product 1

HCID 672490352-(3',5'-Di(docosyloxy)benzyl)-4-methoxybenzyl alcoholYield 94%

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

2-(3′,5′-Di(docosyloxy)benzyl)-4-methoxybenzaldehyde (450 mg, 0.50 mmol) was dissolved in THF-EtOH (4 ml+0.5 ml), sodium borohydride (34 mg, 0.90 mmol) was added, and the mixture was stirred for 3.5 hr. 1N Hydrochloric acid was added dropwise to the reaction mixture to quench the reaction, and the mixture was extracted with chloroform (15 ml), washed once with 1N hydrochloric acid (10 ml), and 3 times with water (5 ml). The solvent was evaporated, and the obtained residue was precipitated with methanol (5 ml) to give 2-(3′,5′-di(docosyloxy)benzyl)-4-methoxybenzyl alcohol (424 mg, 0.47 mmol, 94%).

Workup

  1. customto quench
  2. customthe reaction
  3. extractionthe mixture was extracted with chloroform (15 ml)
  4. washwashed once with 1N hydrochloric acid (10 ml), and 3 times with water (5 ml)
  5. customThe solvent was evaporated
  6. customthe obtained residue was precipitated with methanol (5 ml)

Sources & evidence

ORD record
ord-0d39d276770546cb9756aae3a5adf0f4
Source dataset
uspto-grants-2014_10
Patent number
US08859732B2

Reaction notes

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