Hydrochloric Acid → 4,4'-Didocosoxybenzhydrol

HRID 1754819Notes

Reaction equation

HRID 1754819 reaction equation
[CH2:1]([O:23][C:24]1[CH:60]=[CH:59][C:27]([C:28]([C:30]2[CH:35]=[CH:34][C:33]([O:36][CH2:37][CH2:38][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][CH2:56][CH2:57][CH3:58])=[CH:32][CH:31]=2)=[O:29])=[CH:26][CH:25]=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].C1COCC1.[BH4-].[Na+].Cl>CO>[CH2:1]([O:23][C:24]1[CH:25]=[CH:26][C:27]([CH:28]([OH:29])[C:30]2[CH:35]=[CH:34][C:33]([O:36][CH2:37][CH2:38][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][CH2:56][CH2:57][CH3:58])=[CH:32][CH:31]=2)=[CH:59][CH:60]=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]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 667175264,4'-Didocosyloxy-benzophenone

Product 1

HCID 469361424,4'-DidocosoxybenzhydrolYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To 4,4′-didocosoxy-benzophenone (28.3 g, 34.1 mmol) were added THF (300 mL) and methanol (15 mL) and the mixture was heated to 60° C. Sodium borohydride (6.10 g, 161 mmol) was added slowly, and the mixture was stirred at the same temperature for 4 hr. The reaction mixture was ice-cooled and 1N hydrochloric acid (80 mL) was added dropwise. THF was evaporated, water (450 mL) was added and 1N hydrochloric acid was added to pH 5-7. The slurry was filtered, and the obtained crystals were washed with water and methanol to give 4,4′-didocosoxybenzhydrol (28.5 g, 34.1 mmol, 99%).

Workup

  1. temperaturecooled
  2. customTHF was evaporated
  3. additionwater (450 mL) was added
  4. addition1N hydrochloric acid was added to pH 5-7
  5. filtrationThe slurry was filtered
  6. washthe obtained crystals were washed with water and methanol

Sources & evidence

ORD record
ord-d9a6008221ab43b793d1853b29da7bef
Source dataset
uspto-grants-2015_10
Patent number
US09169187B2

Reaction notes

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