Water → 1,3-Benzenediol, 4-(phenylmethyl)-

HRID 2097247Notes

Reaction equation

HRID 2097247 reaction equation
C(N(CC)CC)C.[OH:8][C:9]1[CH:22]=[C:21]([OH:23])[CH:20]=[CH:19][C:10]=1[C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=O.ClC(OCC)=O.O>C1COCC1>[CH2:11]([C:10]1[CH:19]=[CH:20][C:21]([OH:23])=[CH:22][C:9]=1[OH:8])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 85722,4-DihydroxybenzophenoneHCID 10928Ethyl chloroformate

Product 1

HCID 752941,3-Benzenediol, 4-(phenylmethyl)-

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Triethyl amine (10 ml, 72.2 mmol) was added to a solution of 2,4-dihydroxybenzophenone (1) (5.4 g, 23.3 mmol) in THF (50 ml) and the solution cooled to 0° C. Ethyl chloroformate (6.9 ml, 72.2 mmol) was added slowly and the suspension stirred for ˜30 mins at 0° C., and for ˜3 hrs at room temperature. Water (150 ml) was added and the mixture extracted with diethyl ether (150 ml). The extracts were washed with water (2×150 ml) and saturated aqueous sodium chloride solution (100 ml). The solution was dried over anhydrous magnesium sulphate and concentrated to give 4-benzyl-benzene-1,3-diol as a pale green gum, solidified on standing, (8.2 g).

Workup

  1. waitfor ˜3 hrs at room temperature
  2. extractionthe mixture extracted with diethyl ether (150 ml)
  3. washThe extracts were washed with water (2×150 ml) and saturated aqueous sodium chloride solution (100 ml)
  4. dry with materialThe solution was dried over anhydrous magnesium sulphate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-74500f362b094434a109194e7573a95b
Source dataset
uspto-grants-2013_05
Patent number
US08450310B2

Reaction notes

Loading…